Recent changes to airline 401(k) plans—especially the Roth Nonelective Contribution (NEC) option—have created new opportunities and new confusion for pilots and airline professionals. In this episode, we break down what the Roth NEC actually is, how it works at airlines like Southwest, and why simply ignoring your elections could mean missing out on valuable catch-up contributions.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/y7bncn35

What can last year's markets actually teach us beyond the headlines and noise? In this episode, we look back at the market lessons from the past year to better understand how markets behave and why short-term movements can be so misleading. Rather than trying to predict what comes next, this conversation focuses on learning from what already happened and why diversification remains one of the most powerful tools for managing risk.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/38ftvryn

What if the lessons from 2025 could completely change how you approach the year ahead? In this episode, we reflect on the biggest epiphanies, revelations, and insights gained from our clients, our work, and our own lives last year. You'll learn practical techniques to prioritize what matters most, avoid burnout, and separate your identity from your job. From generosity and communication to asking better questions, this conversation sets the tone for building a meaningful, balanced, and intentional life in 2026.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/y9r6jf2u

What if most individual stocks actually don't outperform and a small handful of massive winners are doing all the heavy lifting? In this episode, renowned finance professor Hank Bessembinder joins the show to break down decades of research on market returns, stock picking, and why diversification matters far more than most investors realize. We unpack his groundbreaking findings on market skewness and explain why identifying winning stocks is far harder than social media and headlines suggest.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/3kef3pdx

What if we're asking the wrong question about market peaks, bubbles, and crashes? Everyone wants to know what happens next, but this episode shifts the focus to what you can actually control: risk, timing, and smart decision-making. Today's conversation breaks down the most common fears investors face — from AI bubbles to gold hype to stock market pullbacks — and gives you a grounded lens for evaluating what's real versus what's noise.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/2d3z463u

What happens when success, identity, and purpose collide with some of the hardest battles a person can face? In this powerful conversation with Ryan Watson, we explore the realities many pilots and high-performing professionals quietly carry: addiction, mental health struggles and the pressure to appear "perfect" in an industry where vulnerability can feel dangerous. Ryan opens up about the challenges he faced, the misconceptions around struggle, and the hidden cultural stigma that keeps so many silent.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/4ahwrx8w

Are private equity and alternative investments really the secret weapon of the wealthy or are public markets still your best bet? In this episode, we tackle one of the most common questions we hear: should you look beyond the stock market? We'll break down what private equity really is, who it's for, and why some companies stay private instead of going public. You'll learn how these investments work, why they're not always the golden ticket they appear to be, and how to think critically about diversifying your portfolio.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/2eyuv9n8

Why do airlines struggle to make money even when planes are full? In this episode, we unpack the surprising economics behind one of the world's most essential yet fragile industries. From razor-thin profit margins to the ripple effects of global shocks like COVID-19, you'll learn why airlines operate on such precarious financial ground and what it takes for them to stay in the air.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/ypwpywzf

What do the new Secure Act 2.0 rules mean for Roth contributions and retirement planning in 2025? In this episode, we explore what pilots and high-income earners need to know about Roth catch-up contributions, required Roth designations, and the risks of in-plan Roth conversions. You'll also learn how these changes may impact your taxes, your long-term retirement savings, and the best ways to prepare now.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/2f6srj8e

What actually makes for a happy, fulfilling retirement? Is it all about the numbers, or is there more to the story? In this episode, Dr. Michael Finke—professor, researcher, and one of the most respected voices in retirement planning—shares his groundbreaking research on what truly drives satisfaction in retirement. Drawing from decades of data, interviews, and insights from retirees themselves, Dr. Finke uncovers the three essential pillars of a rewarding life after work.

Take The Pilot Wealth Index to find out if you are on track for retirement!

You can find show notes, resources and more at: https://tinyurl.com/bwvxsd69